58 days in Chicago & New York City Itinerary

58 days in Chicago & New York City Itinerary

Created using Inspirock United States journey maker

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Chicago
— 23 nights
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2
New York City
— 33 nights
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Chicago

— 23 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore hidden gems such as Food Tours and Lake Michigan. Explore Chicago's surroundings by going to Moraine Park (in Highland Park), Westclox Museum (in Peru) and Starved Rock State Park (in Utica). Next up on the itinerary: appreciate the extensive heritage of Chicago Riverwalk, admire the local landmark of Buckingham Fountain, see the interesting displays at Harley-Davidson Museum, and get curious at Field Museum.

For photos, other places to visit, maps, and more tourist information, read our Chicago road trip planner.

Ho Chi Minh City, Vietnam to Chicago is an approximately 22.5-hour flight. You'll gain 13 hours traveling from Ho Chi Minh City to Chicago due to the time zone difference. Traveling from Ho Chi Minh City in June, expect Chicago to be slightly colder, temps between 32°C and 20°C. Cap off your sightseeing on the 17th (Sat) early enough to catch the flight to New York City.

Things to do in Chicago

Parks · Museums · Outdoors · Historic Sites

Side Trips

New York City

— 33 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
You'll explore the less-touristy side of things at Food Tours and Photography Tours. Change things up with these side-trips from New York City: Hyde Park (Vanderbilt Mansion National Historic Site, Home of Franklin D. Roosevelt, &more), Poughkeepsie (Walkway Over the Hudson State Historic Park & Calvary Chapel of the Hudson Valley) and Philadelphia (Independence National Historical Park, Rodin Museum, &more). There's lots more to do: go for a walk through Central Park, race across the water with a speed boat tour, explore the world behind art at The Metropolitan Museum of Art, and get the lay of the land with Walking tours.

Inspirock's itinerary builder makes planning a New York City trip simple and quick.

You can fly from Chicago to New York City in 4 hours. Other options are to drive; or take a bus. The time zone difference when traveling from Chicago to New York City is 1 hour. In July in New York City, expect temperatures between 35°C during the day and 26°C at night. Wrap up your sightseeing by early afternoon on the 19th (Thu) to allow time for the flight back home.

Things to do in New York City

Parks · Historic Sites · Museums · Neighborhoods

Side Trips